The present invention is related to compounds of the formula ##STR2## wherein Ar is an optionally substituted 5-8 membered heteroaryl or optionally substituted benzene fused optionally substituted heteroaryl ring wherein said heteroaryl ring comprises 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur;
and pharmaceutically acceptable salts and prodrugs therefor (hereafter "the active compounds"). PA1 a) treating the compound of the formula ##STR5## with L-Selectride (trademark) commonly known as lithium tri-sec-butyl borohydride or NaBH.sub.4 and CeCl.sub.3, to form the compound of the formula ##STR6## and treating the compound of formula IVB with (R) camphorsulfonic acid, [(R)-CSA], ##STR7## b) 1) treating the compound of the formula IVA with a base, preferably Na.sub.2 CO.sub.3, to again form the the compound of the formula IVB and ii) treating the compound of formula IVB formed in this step, with ditoluyl-L-tartaric acid [L-DTTA] to form the compound of the formula ##STR8## or 2) treating the compound of formula IVA with hot acetone to isolate the compound of the formula ##STR9## and c) treating the compound of formula IIIB or IIIC with a base to form the compound of the formula ##STR10## and then treating the compound of the formula IIID with H.sub.2 over a noble metal catalyst, preferably Pd(OH).sub.2, to form the compound of formula II.
More particularly it relates to processes and intermediates useful in the preparation of the compound of the formula ##STR3## which are intermediates useful in the preparation of compounds of the formula I.
The active compounds, which are disclosed in International Patent application no. PCT/US93/09171 (the '171 application) (assigned to the Assignee of this application and incorporated herein by reference), inhibit the production of leukotrienes and/or block leukotriene receptors and are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals.
U.S. Pat. No. 4,661,596, refers to compounds which are disubstituted naphthalenes, dihydronaphthalenes or tetralins having the formula ##STR4## wherein the dotted lines represent optional double bonds, R.sup.a is 2-pyridyl, 2-quinolyl, 2-pyrazinyl, 2-quinoxalinyl, 2-thiazolyl, 2-benzothiazolyl, 2-oxazolyl, 2-benzoxazolyl, 1-alkyl-2-imidazolyl or 1-alkyl-2-benzimidazolyl and R.sup.b is hydroxy, lower alkoxy, lower alkyl or perfluoro alkyl.
U.S. Pat. No. 5,059,609 refers to substituted tetralins, chromans and related compounds.
The compounds of these patents are alleged to inhibit lipoxygenase enzyme and antagonize the effects of leukotriene D4 and, therefore, to be useful in the prevention and treatment of asthma.